This is Halloween
by Kingpin1055
Summary: For Jackson Overland, Halloween is one of his favourite nights of the year, and although he pulls out all of the stops to ensure his sister and her friends have a evening full of treats, he rarely ends the evening with any treats of his own... That is until he meets Hamish Haddock.


Jack was smiling, this was one of the best nights of the year, and tonight... He was the Pumpkin King.

It was no secret to Jack Overland's friends and family that Halloween held a special place in his heart, he'd gone trick-or-treating from when he was first old enough to go out into the night with his father, and he'd continued until some of his neighbors had started politely remarking to an adolescent Jack that maybe he was outgrowing the activity.

After his dad passed away, well... He found himself immersed in the holiday once more through filling the role of his father, Robert Overland, in order to take his little sister out into Burgess for a night of ghoulish fun.

The year of the elder Overland's death had been hard, and it'd been one of the few years Jack had not felt the spirit of the holiday, but Olivia had pleaded with him to go out, and it was thanks to her that he rediscovered his love for the 31st of October.

And as it happened, he'd collected some strays along the way.

"I'd like them back by no later than seven-thirty, it may be Halloween but it's still a school night."

"It won't be a problem Mrs. Bennett." Jack responded with a somber nod.

Catherine Bennett gave Jack, his sister, and her children a fond smile. "Listen to Jack when he tells you something, don't wander off, don't talk to anyone you don't know... And have fun. Happy Halloween."

"Happy Halloween!" Sophie Bennett cheered back, dressed as a fairy in an iridescent costume of green and violet.

"Thanks, Mom." Jamie smiled; he was dressed as the Green Paladin of Voltron.

"Happy Halloween, Mrs. Bennett." Olivia smiled, attired as Wonder Woman.

"Hope you have a fun evening with your brother." Catherine waved, and was able to enjoy a moment to watch them cross the front lawn to the sidewalk, before she was greeted by another group of trick-or-treaters.

"Alright, I know you guys are looking to rake in an awesome haul tonight so here's what I think we should do: we go up and down Chestnut Street, Franklin and Oak, hitting every house we can, and if we're quick, we might be able to do Gilmore and Barclay Streets in between."

Jamie and Sophie looked excited at the prospect, Olivia appeared skeptical.

"We're not going to be able to visit all of those houses in that time, Jack."

"Ye of little faith! Halloween's the night where time stretches and night lives forever." He turned back to his more enthusiastic companions. "Now, who wants to score some free candy?!"

The elated chorus was more than enough to put them in the mood for the evening, and with their plastic pumpkin buckets in tow, the group led by Skeleton Jack ventured out into the gathering twilight.

* * *

The wick sparked into life with the help of the lighter, illuminating the last Jack-o'-lantern that Hamish Haddock had spent the afternoon carving with his best friend, Astrid Hofferson. He admired his craftsmanship, before he gave the front of the house one last look-over. There was a generous, but not over-the-top trimming of decorations across the porch and the front lawn: fake cobwebs were strung across the obvious spots on the porch pillars and railings, plastic gravestones were scattered in a deliberately haphazard fashion in the grass (complete with cosmetic overgrowth), and a couple of fog machines had been hidden in the rose buses at the base of the porch for atmosphere.

Hamish always had more ideas in mind, but he made an effort to scale them back to what he could realistically get his Dad to agree to.

And with the senior Police Officer currently on duty to take care of any Halloween pranks that might go awry, he had the house to himself with his blonde-haired companion, who was currently tucking into some Twizzlers she'd snuck out of the bowl of treats.

He shook his head in admonishment. "Those are for the callers, I've stashed you a bag inside."

"Correction, you _did_ stash a bag." His expression clearly announced his displeasure, she shrugged in response. "You need a better hiding spot."

He let out a frustrated sigh. "Duly noted. But _that's_ your last one for tonight."

She finished off the last bit of the Twizzler she'd been chewing. "I make no promises."

As they stepped into the house, Hamish flicked on the porch light and smirked. "Show time."

He was dressed in a home-made Star-Lord costume, and she'd gone to some effort to wear something analogous to Link from the _Legend of Zelda_ series, costumes that they'd be comfortable enough wearing whilst watching television in the time between greeting trick-or-treaters.

Hamish checked over the bowl of candy as Astrid fired up the television, popping in the DVD of the 1982 version of _Poltergeist_. A film they'd seen enough times to be able to watch casually, and not mind missing parts during the evening.

They'd only just gotten past the introduction of the Freelings and their haunted house, when the doorbell rang with the first gaggle of children of the night.

* * *

By the time they'd finished Chestnut Street, night had fully fallen on Burgess, and most of the houses were aglow with ghoulish decorations, strings of lights, and animated projections. Flashlights and blinking costume accessories filled the dark spots between the streetlights as children and adults made their way from one house to the next, whilst the air was awash with the excited chatter of children and the jovial conversation of their elders.  
In some areas the rabble was accompanied by themed music, ranging from popular commercial songs, to cheesy dollar store Halloween compilation albums.

Jack's charges were just checking the spoils they'd acquired from a house that was broadcasting a lame cover of _The Monster Mash_ , the snickers Jamie and Sophie had received, and the Mars bar Olivia had been given because of her allergy, made up for the disappointing audio choice.

He could feel the air of excitement buzzing amongst them, they'd already gotten a pretty good selection of sweets as they'd made their way along the street, but one of the houses that waited for them around the corner of Barclay Street was one the kids always went out of their way to visit: the residence of Nicholas Severnaya. Whilst it was his Christmas decorations that had made Nicholas a local celebrity, he was no slouch when it came to All Hallows' Eve.

"How you guys feeling? Anyone starting to get tired?" The white-haired man playfully questioned. The three enthusiastic protests of 'No!' were all the proof Jack needed that they had plenty of walk still in them. "Okay, okay... So anyone know whose house we're getting near?"

"Nick's!" Olivia cheered in realization.

"Awesome!" Jamie grinned broadly as Sophie let out an excited giggle. Without any further encouragement, they took off at a determined pace.

* * *

Like previous years, Nicholas Severnaya's house was not a disappointment when it came to decoration. An animated array of rope lights highlighted each window of the property, and a selection of spooky faces were singing away. The music was being played at a respectful volume, loud enough to be heard, but not too high to make the neighbors unhappy. In addition to the concealed speakers, the soundtrack that the lights were timed to was broadcast wirelessly to any cars passing by that happened to be tuned in.

 _"_ _I always feel like somebody's watching me_  
 _And I have no privacy  
Woh, I always feel like somebody's watching me  
Tell me is it just a dream?"_

The quartet marched up the brick pathway, the route marked by skeletal arms clasping glowing lanterns.

Jamie reached for the knocker on the door, and jumped when it suddenly screeched at him.

The front door swung open, and the party was greeted by the rosy, smiling face of Nicholas Severnaya, tailored this year in the attire of Captain Spaulding from _House of 1000 Corpses_ , although the costume easily served the role of 'creepy clown', as Jack was the only person in the gathering who was old enough to understand the reference. " _Schastlivogo Khellouina_! Happy Halloween!" Nicholas greeted. At his side was his friend Ana Fisher, attired in a faithful Morticia Addams gown.

"Hey everyone." she smiled with a wave.

Nicholas took on a studious air, giving each of the children a careful appraisal. "Would you three be Sir Gawain, a Spartan warrioress, and a pixie?"

Sophie's proud smile could've lit the night by itself. "I'm a fairy!" she beamed.

"So you are, sweetie." Ana nodded.

Jamie struck a defiant pose. "I'm Jamie Bennett, the Green Paladin of Voltron."

"And brave defender of the universe you are." Nicholas noted with a salute.

"I am Princess Diana of Themyscira, sworn member of the Justice League of America." Olivia announced proudly, bearing her sword aloft and brandishing her shield.

"Your armor looks fantastic, did you make it yourself?" Ana enquired.

"Jack helped me make it more accurate." Olivia explained.

"And of course, the Pumpkin King himself needs no introduction!" Nicholas smirked, provoking Jack to perform a theatric bow.

"You flatter me, good sir!" Jack returned in a playful tone. "You guys have outdone yourselves again this year."

"We try." The Russian noted with a playful tone. "Now I fear I am being bad host in keeping you from your treat!" Nick announced with a clap of his hands. The sinister clown produced a generously-stocked box decorated like a blood-splattered crate. "Help yourselves."

As the children made their selections from the offered sweets, Ana quietly snuck some floss into each buckets they held.

"What do we say to Nick and Ana?" Jack prompted.

"Thank you!" the three children cheered and the two adults beamed back.

"You are most welcome." Nick nodded.

"Have a greet Halloween, guys. And don't forget to floss!" Jack chuckled as the group made their way back towards the sidewalk. He offered Nick and Ana one final wave before they slipped from sight.

* * *

By the time Carol Anne was sliding across the kitchen floor, and the breakfast nook chairs were stacking themselves, Hamish and Astrid had served a pretty steady stream of trick-or-treating families.

The experiences had been fun, and Hamish's interest in costume making had made him more animated than usual as he talked to the kids who'd made their own costumes. The fun could never last, and the moment came in the form of a pair of mischievous twins, a young man and a young woman who needed little introduction: Rebekka and Tomi Thorston. The twins were dressed respectively as Joker and Harley Quinn from _Suicide Squad_ (which was just a tad creepy).

"'Trick-or-treat, smell our feet, give us something nice to eat'." they sang in unison.

"Hey guys." Astrid greeted, Hamish admired how convincingly genuine she sounded.

"Hey." He responded in a much less convincing tone.

"So what're you guys watching this year? _Halloween_? _Friday the Thirteenth_? _Nightmare on Elm Street_?" Rebekka enquired.

" _Poltergeist_." Astrid supplied.

"The one with the guy out of _Iron Man Two_?" Tommi recalled.

Hamish shook his head. "The original one, from the nineteen-eighties."

Tommi smiled and nodded his head in approval. "Rock on, 'go into the light Carol Anne'!"

Hamish wasted little time giving them some treats, including a bit extra effectively as a bribe. He'd quickly learned that sometimes you just gave the Thorstons an extra chocolate bar if it saved your house from being decorated in egg yolk.

"See you guys later." The man dressed as Star-Lord remarked, with a more genuine smile this time.

"Laters!" Tommi fired back.

"We're gonna go egg old Mildew's place next." Rebekka added joyfully.

"Throw one for me!" Astrid requested with a bright smile, her voice was laden with mirth. Few people around town were fans of the resident killjoy and notorious grouch.

"We'll throw one for each of you!" Tommi shouted back as they continued their journey up the street.

Hamish let out a breath of relief as the twins melted back into the night. "And _that's_ over for another year."

"They've got you whipped." She quietly laughed.

"Don't hold it against me; you've not experience Hell until you've had to clean the sort of mess they can make with eggs, toilet paper, toothpaste and washing up liquid."

She grimaced at the possibilities he'd conjured up. Her attention was then caught by an approaching group of children, stewarded by a single adult.

"You've got some more customers."

The auburn-haired boy turned his attention to the new arrivals, taking particular note of the guy dressed as Jack Skellington.

* * *

A pair of teenagers dressed like Joker and Harley Quinn from _Suicide Squad_ chuckled in an unsettling fashion as they galloped across the front lawn of the house Jack and the kids were approaching. He hoped they were just really in character, but he recognized something in the tone which told him they'd be up to no good tonight (the dubious talent which resulted from a somewhat misspent youth, you could recognize your own kind - his 'playdar' as he liked to call it).

The people living at the house had made a reasonable effort, there was a small, fog-infused cemetery populating the front lawn, whilst carved pumpkins and fake spider webs carried the festivities onto the front of the house itself.

The door was already open as Jamie and Sophie lead the pack in a walk among the tombstones, and a guy dressed as Star-Lord readied what appeared to be a bowl of candy as a woman dressed as Link greeted them with a playful swish of her Master Sword.

"Trick-or-treat!" the children greeted in earnest.

"You guys look amazing." The guy with the candy remarked with an impressed grin. Jamie looked as pleased as punch, whilst Olivia smiled back in return.

Emboldened by the praise, Sophie spun around the group for a few loops, letting out a loud "I'm a fairy, _wheeeeeeee_!" as she did.

Star-Lord handed out some candy from the bowl he was holding, before he glanced at Jack. "Nice work on the face paint, Pumpkin King."

Jack shrugged. "'There are few who deny at what I do, I am the best.'" He responded with a smirk.

"'For your talents are renowned far and wide.'" The other young man responded in kind. Jack hadn't expected the guy to sing the next verse of _Jack's Lament_.

"Jack." he held out his hand.

The other guy gave him a bemused smile, but he accepted his hand anyway. "I know."

"No, I mean... My name's really Jack."

"Oh!" The other guy looked sheepish for a moment. "Hamish. Ah... My name's Hamish."

There was an air of something between them, not awkward, but unexpected. He wanted to pursue it further, but the children were already moving, and their eyes were trained on him.

"C'mon Jack!" Jamie called.

The Pumpkin King returned his attention to Hamish briefly. "Uh... Nice meeting you... Hamish."

The other young man seemed to be experiencing something similar, as his reply was also muddled. "Yeah, um... See you around, Jack."

The chaperone spared one final look, and a wave that he half regretted as soon as he'd thrown it, before the impatient remarks of Jamie snapped him back to his immediate reality.

* * *

Astrid had rolled her eyes as soon as the air between Hamish and Jack had manifested, and as soon as Skeleton Jack had vanished from view, she gave her best friend a half-hearted bump to the arm.

"You've got it _so_ bad."

With no place he could easily retreat to, and caught under the intense scrutiny of her blue eyes, Hamish had the good decency to become flustered. "It was just a moment, barely even a moment... And probably nothing. Besides, I don't know who he is or where he lives, so I probably won't see him again."

She crossed her arms over her chest. "I can watch over the house if you want. You can still catch up with him."

He genuinely looked like he was considering her offer, before he let out a puff of air in defeat. "No, it wouldn't be fair on you to leave you here."

Despite his rationale behind the decision, he did wish he could just drop what he was doing and chase about the boy with the skeleton face.

* * *

Jamie, Sophie and Olivia had gotten a good haul, they'd managed to cover the whole route Jack had suggested, and were now making their way back, now that the clock on his cell phone showed that it was nearly a quarter past seven in the evening. Although his charges were jubilant at the treats they'd received, he felt a little hollow in sharing their celebration. He'd found his thoughts going back to Hamish.

Olivia's voice snapped him out of his brooding: "Are you okay? You've been really quiet."

"What, me? I'm better than fine." he rebuffed, and he internally winced at how unconvincing he was.

"You're thinking about that guy in the space costume, aren't you?"

"Well, yeah... It's not easy to make a costume like that."

She responded with a look that made her seem wise beyond her years.

He rolled his eyes in defeat. "Alright, so maybe I would've liked to spent longer talking with him... But tonight's about you guys."

"You've been taking us out for Halloween for three years now; you're allowed to have a little fun yourself."

"You guys are enough fun for one night." He remarked brightly.

She shook her head ruefully, embodying the unique dynamic of the Overland children: the elder brother who acted younger than his little sister, and the sister who was frequently more mature than her older brother. "You need help. Why don't you say to Mom 'Hey mom, I'm gonna go out and meet some friends for a bit' when she picks us up later?"

It wasn't a bad idea, actually. "I'll think about it." He proposed, and ruffled her hair. The Bennett House crept into view along the sidewalk, and he tried to banish his lingering preoccupation with Hamish.  
The quartet pushed through the gate leading into the Bennetts' back yard, and after a brief ascent up the steps of the rear porch of the house, Jack stuck his head inside to see Mrs. Bennett in the middle of a conversation with his mother.

Emily Overland was the first to spot them; she broke into a smile, which alerted Catherine to their arrival.

"Happy Halloween Jamie, Sophie." the brunette greeted warmly as the children surged into the kitchen. "Did you have a good night?"

"We sure did!" Jamie chimed in. "We got _sooo_ much candy!" he held up his plastic pumpkin for her to see.

"Oh! Oh! Look what I got!" Sophie cheered beside her older brother, holding up a similarly-sized trove.

Mrs. Bennett shook her head in playful reproach. "You can have some tonight, and save the rest for tomorrow."

Jamie looked a bit dejected, but nodded obediently. "Yes Mom."

"Head on into the living room, we might just have time to squeeze in _Coraline_ before you have to get ready for bed."

Jamie brightened at that prospect, and he quickly followed his sister towards the front of the house. Catherine turned her attention to Emily and her children. "Would you like to stay for the film?"

"I think we can make an exception." Emily smiled. "Would you two like to stay for the film?"

"Sure." Olivia beamed, and she then winked conspiratorially at Jack.

Jack considered his sister's suggestion, and the moment of hesitation prompted Emily to adopt a look of concern. "Everything okay, 'Frosty'?"

She usually only broke out Jack's childhood nickname in times where she thought he needed someone who would listen to whatever he would say, and give her best advice when Jack needed support or guidance. It rarely failed to aid him in lowering his defenses, and had been forged due to his affinity for snow and winter.

He shifted under her gaze. "Would it be okay if I head out for a bit? I was talking to someone a little earlier and I wanted to see if they wanted to hang out for a little longer tonight?"

Emily's concern melted from her face, although there was still a part of her that wasn't completely certain, based on the tone of her son's voice, and his posture. It'd been a while since she'd seen him look so nervous.

"Of course you can. Do you have your keys?"

"Yeah." He extracted them from his trouser pocket and held them out for her to see. She nodded in acknowledgement.

"I hope you have fun with your friend, just don't be _too_ late home, please. You may be eighteen, but you still have work in the morning."

Jack was more his regular self when he smiled, offering her a cocky grin in response. "Yes ma'am."

Shaking her head in playful resignation, Emily Overland and Catherine Bennett followed Jack to the front door of the house, and watched as he quickly dashed across the front yard and onto the sidewalk.

"I've never seen him look so nervous, Jack's usually so confident." Catherine mused aloud.

"He usually is, but there are times... Often when he's talking about someone he's got a bit of a crush on, where he gets nervous. That's my feeling on it anyway; I think if he was just going to meet up with one of his friends, he would've said who it was."

A brief wash of surprise enveloped Mrs. Bennett's face. "Is Jack dating someone?"

"Not at the moment as far as I'm aware... But maybe if tonight goes well..." She smiled fondly. "Maybe the Pumpkin King will find his prince."

* * *

The clock on the mantelpiece quietly announced the arrival of 8:15pm, and it looked like the evening was quieting down. Astrid and Hamish hadn't had a trick-or-treater call on them in nearly a quarter of an hour, and a few cursory glances up and down the street revealed it to be devoid of any child activity.

Sensing that they'd had the last of the crowds for the night; Hamish had extinguished the Jack-o'-lanterns and porch light, and had retired on the couch with Astrid so they could watch the last of _Poltergeist_.

The end credits were rolling when the doorbell rang, and the auburn-haired teenager glanced warily towards the door.

"We could just ignore them." Astrid suggested.

He scratched his chin in as he considered the suggestion, but ultimately chose to dismiss it. "It's okay, if it's some kids I'll give them what's left in the bowl."

He unlatched the door and peered through the gap he'd opened, only to pull it open further in response to who was stood on his doorstep.

He did his best to hide his surprise with an air of aloofness. "Don't you know Halloween protocol? If the porch light's off, we're not giving anything out."

"You really sure you want to risk getting a trick?" Jack smirked in the gloom.

"You don't scare me; I've been tricked by the Thorstons before."

The Pumpkin King grimaced. "Yikes."

"Yeah." Hamish nodded. "So how can I help 'Jack Skellington'?"

Jack offered him a relaxed smile. "I was kinda wondering if you might want to meet up some time? I would've asked earlier, but I'd promised the kids I was looking after that we'd get a lot of candy tonight."

Hamish leant against the doorframe, a note of bemusement on his face. "I don't know, you've already admitted you're a sugar dealer... It might be setting a bad example to date someone _so_ irresponsible." He noted playfully.

"I'll turn myself in to the cops if it makes things easier for you." Jack laughed, holding his hands out in front of him as if waiting to be handcuffed.

"Maybe." Hamish smirked, and the smirk then softened into a friendly smile. "My friend and I were just about to watch a DVD, you want to join us?"

Jack beamed. "Sure. What are you guys watching?"

"We hadn't decided yet... how does _The Nightmare Before Christmas_ sound?"

"I see what you did there." the face-painted man grinned. "'My newest friend, if you don't mind. I'd like to join you by your side'."

Jack's grin grew at the caught off-guard look on Hamish's face. The other man regained his composure, and sang back: "'And sit together, now and forever'... or at least until my Dad gets home."

"Sounds good."

Hamish stepped aside to let Jack into the front hall; he'd only just closed the front door when Astrid revealed she was sat on the bottom step of the staircase, petting Toothless who was now eyeing Jack warily.

"That was really corny."

Both young men looked startled. "The only thing corny tonight is candy corn, and we don't have any of that here." He suddenly glanced at Hamish. "You don't have any of that, right?"

Hamish almost looked appalled. "Oh Gods no."

Jack let out a relieved puff of air. "Great."

"You okay with watching _The Nightmare Before Christmas_?" The auburn-haired teenager checked with the blonde girl.

She shrugged. "I'm good with it, as long as you guys don't duet _every_ song." Astrid requested as she rose from where she'd been sitting, and headed into the living room with Toothless in tow.

The three teenagers and Norwegian Forest cat settled onto the couch in front of the television. As Astrid booted up the DVD, Hamish nudged Jack.

"Hamish Haddock."

Jack nudged back. "Jack Overland."

Hamish smiled fondly for a moment, before he raised the bowl of left-over candy so they could dig through the remains of the night.

Santa Claus's opening narration served as background noise, they only turned to watch the screen when Danny Elfman's dramatic strings began to seep out of the speakers.

"'Boys and girls of every age  
Wouldn't you like to see something strange?

Come with us and you will see  
This, our town of Halloween...'"

"'This is Halloween, this is Halloween. Pumpkins scream of the dead of night!'" Hamish and Jack sang in near-unison. "'This is Halloween, everybody make a scene. Trick or treat till the neighbors gonna die of fright! It's our town, everybody scream! In this town of Halloween!'"

The two young men broken into laughter, before a half-hearted withering glare from Astrid had them settling down.

"Happy Halloween." Jack whispered as the residents of Halloween Town finished their grand opening.

There was amusement in Hamish's voice as he responded: "Happy Halloween."

* * *

 **The End**


End file.
